Triethylamine → tert-butyl-N-[1-[[5-(3,5-dimethylpyridin-4-yl)-6-(2-quinolin-6-ylethynyl)-pyridin-2-yl]amino]-1-oxopropan-2-yl]-N-methylcarbamate

HRID 535408ノート

反応式

HRID 535408 の反応式
[C:1]([O:5][C:6](=[O:30])[N:7]([CH:9]([CH3:29])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:24]([CH3:25])=[CH:23][N:22]=[CH:21][C:20]=2[CH3:26])=[C:15]([C:27]#[CH:28])[N:14]=1)=[O:11])[CH3:8])([CH3:4])([CH3:3])[CH3:2].I[C:32]1[CH:33]=[C:34]2[C:39](=[CH:40][CH:41]=1)[N:38]=[CH:37][CH:36]=[CH:35]2.C(N(CC)CC)C>CN1C(=O)CCC1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:5][C:6](=[O:30])[N:7]([CH:9]([CH3:29])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:20]([CH3:26])=[CH:21][N:22]=[CH:23][C:24]=2[CH3:25])=[C:15]([C:27]#[C:28][C:32]2[CH:33]=[C:34]3[C:39](=[CH:40][CH:41]=2)[N:38]=[CH:37][CH:36]=[CH:35]3)[N:14]=1)=[O:11])[CH3:8])([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 203985536-IodoquinolineHCID 86694395tert-butyl-N-[1-[[5-(3,5-dimethylpyridin-4-yl)-6-ethynylpyridin-2-yl]amino]-1-oxopropan-2-yl]-N-methylcarbamate

生成物 1

HCID 86694394tert-butyl-N-[1-[[5-(3,5-dimethylpyridin-4-yl)-6-(2-quinolin-6-ylethynyl)-pyridin-2-yl]amino]-1-oxopropan-2-yl]-N-methylcarbamate

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

A mixture of tert-butyl-N-[1-[[5-(3,5-dimethylpyridin-4-yl)-6-ethynylpyridin-2-yl]amino]-1-oxopropan-2-yl]-N-methylcarbamate (E1a desilylated according to the general method exemplified for F1a) (50 mg, 0.12 mmol), 6-iodoquinoline (89 mg, 0.35 mmol), copper(I) iodide (2.2 mg, 0.01 mmol), Dichlorobis(triphenylphosphine)palladium(II) (8.1 mg, 0.01 mmol) and triethylamine (64 μl, 0.47 mmol) is stirred under argon atmosphere in NMP (0.5 ml) for 1 h at 50° C. The mixture is concentrated in vacuo and the product purified by RP HPLC. Yield: 28 mg (45%). HPLC-MS: M+H=536; tR=1.79 min (*Method—3).

後処理

  1. concentrationThe mixture is concentrated in vacuo
  2. customthe product purified by RP HPLC

出典と根拠

ORDレコード
ord-3c314ccc49a247e7b012b09d4cceadea
出典データセット
uspto-grants-2014_10
特許番号
US08859541B2

反応ノート

読み込み中…